Sciencemadness Discussion Board - Was shipped wrong item, got a bottle of glucose instead of choline chloride. Anything cool I can do with glucose?

Was shipped wrong item, got a bottle of glucose instead of choline chloride. Anything cool I can do with glucose?

Cou - 17-4-2020 at 18:32

It was only $7 and dont wanna go thru the hassle of amazon returns.

Im currently in biochemistry I. What kind of organic reactions can I do with glucose? Cleavage of the cyclic hemiacetal bond to form linear glucose? It has a ton of alcohol groups. If I oxidized with dichromate, would I get some weird compound like a carbon chain with a ketone group at every carbon of the chain? Could I do a fisher esterification with acetic acid to acetylate every hydroxyl group?

[Edited on 18-4-2020 by Cou]

[Edited on 18-4-2020 by Cou]

dawt - 17-4-2020 at 21:20

Anything drastic (i. e. Fischer esterification etc) is going to yield you tar and a whole bunch of dehydrated products. Sugar chemistry tends to be really messy even under the best circumstances. If you want to isolate any product I'd look into enzymatic reactions instead! Depending on which enzymes you can get your hands on you can make all sorts of useful stuff: Check out glycolysis amd the Krebs cycle.

Otherwise I'd get a couple of amino acids and do some Maillard reactions in test tubes. Vary the reaction conditions, e. g. temperature, pH, solvent (or no solvent at all) and note the differences in smell, reaction rate etc.

Edit: Since glucose is a reducing sugar you might also want to test it on some inorganics and see which ions it can mess with. This could yield you anything from gluconic acid to carbon dioxide, depending on the oxidising power of your ion under the selected conditions.

[Edited on 2020-4-18 by dawt]

j_sum1 - 17-4-2020 at 21:39

If you have never done the blue bottle reaction, you should. And there are some variants.
The manganese chemical chameleon works differently with glucose instead of sucrose. That might be a worthy investigation.
You might try polymerisation. You aren't going to get anything that you can analyse but I bet you could find something interesting and quantifiable.
Then there is tons you could do biologically.

clearly_not_atara - 17-4-2020 at 22:06

Reduction of glucose gives sorbitol.

Sorbitol can then be converted to sorbitan or isosorbide by acid-catalyzed dehydration. These are much more "well-behaved" chemicals that can become a number of things.

Cou - 18-4-2020 at 03:28

actually the bottle was sucrose, not glucose. I was a little frustrated at wrong item and set the bottle at front door, didn't check name thoroughly.

unionised - 18-4-2020 at 04:06

Fermentation and distillation?

brubei - 18-4-2020 at 06:26

acidic hydrolysis of glucose yield to Hydroxymethylfurfural, a flavouring agent (but do not eat it !)

https://en.wikipedia.org/wiki/Hydroxymethylfurfural

Texium - 18-4-2020 at 08:31

Wow, sucrose, that's about as disappointing as it gets from a chemistry standpoint. I think unionised's suggestion is the most practical. That, or combine it with butter, eggs, and flour with a catalytic amount of sodium bicarbonate and synthesize some cookies!

clearly_not_atara - 18-4-2020 at 08:56

You can make levulinic acid from sucrose!

But you should complain. You bought a high value product and they sent you something cheap. Glucose is at least kind of interesting.

Cou - 18-4-2020 at 09:25

Name of the company is HiMedia. they are an amazon seller that i have bought propionic acid and benzophenone from, prime delivery, but this time they messed up and they have bad customer service.

https://www.amazon.com/gp/product/B00DYO6706/ref=ppx_yo_dt_b...

Texium - 18-4-2020 at 10:15

Interestingly when you look at the reviews, they apparently had people experiencing almost the exact opposite problem!

Screen Shot 2020-04-18 at 1.14.03 PM.png - 179kB

Edit: those are the only two reviews. Presumably, the item listing used to say gum acacia powder, and it was changed to choline chloride later.

[Edited on 4-18-2020 by Texium (zts16)]

mackolol - 18-4-2020 at 10:43

What did you want to make from choline chloride, was it more available form of choline such as alpha gpc or cdp-choline?

Cou - 18-4-2020 at 10:59

Quote: Originally posted by mackolol

What did you want to make from choline chloride, was it more available form of choline such as alpha gpc or cdp-choline?

A mixture of choline chloride and glycerin can be used to extract alcohol from impure ester, e.g. the mixture of 1-nonanol and nonyl acetate after working up a fischer esterification. Just mix with the deep-eutectic solvent, the pure ester separates from the DES/alcohol layer. https://www.sciencedirect.com/science/article/pii/S004040391...

in a thread in the organic chemistry forum i brought up a problem with synthesis of esters from acetic acid and long chain alcohols by fischer esterification: even with a large excess of acetic acid, the reaction doesn't use up all the alcohol. long alcohols like 1-nonanol can't be extracted with water, can't be separated by distillation, and they contaminate the smell of the ester.

Using acetic anhydride or acetyl chloride is one way to use all the alcohol, but they are both hard to get, expensive, and doesn't solve the problem for formate esters since formic anhydride and formyl halides are both unstable.

the steglich esterification goes to completion, but choline chloride and glycerin are more readily available and cheaper than the catalysts used in steglich esterification. Industry prefers fischer esterification because the lower yield outweights the cost of reagents that can esterify to completion.

The dean-stark method doesn't work for making acetate esters, since acetic acid and toluene form an azeotrope below the boiling point of toluene.

I think the best way to do this is to do a fischer esterification with large excess of acetic acid (a very cheap chemical) and purify the crude ester with the deep eutectic solvent.

[Edited on 18-4-2020 by Cou]

mackolol - 19-4-2020 at 02:28

Very interesting and very useful Cou, thanks for sharing. I didn't know that.

Metacelsus - 19-4-2020 at 05:28

Quote: Originally posted by Cou

Name of the company is HiMedia. they are an amazon seller that i have bought propionic acid and benzophenone from, prime delivery, but this time they messed up and they have bad customer service.

I've bought stuff from them before (crystal violet and EDTA). Too bad they messed up your order.

Dr.Bob - 19-4-2020 at 07:57

I would use it in coffee... Just sedn them a note and ask them to fix it. Any reasonable company will fix their mistake, if not, file a complaint or leave more bad feedback. That will keep them from messing up others.

Cou - 19-4-2020 at 11:37

Just received choline chloride. it has a weak fishy amine odor. $30 for this bottle of 500 g, but it's still a lot cheaper than the chemicals used in esterification reactions that go to completion, such as steglich esterification and using acid chlorides, anhydrides.

[Edited on 19-4-2020 by Cou]

CharlieA - 19-4-2020 at 17:02

Quote: Originally posted by Texium (zts16)

Wow, sucrose, that's about as disappointing as it gets from a chemistry standpoint. I think unionised's suggestion is the most practical. That, or combine it with butter, eggs, and flour with a catalytic amount of sodium bicarbonate and synthesize some cookies!

I can go with the cookies, or a cake. Or just use it to sweeten your tea or coffee